Diethyl Oxalate → HCID 86711957, compound

HRID 1475266Notes

Reaction equation

HRID 1475266 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[C:15](OCC)(=[O:21])[C:16]([O:18][CH2:19]C)=[O:17].C[O-].[Na+]>CO>[O:21]=[C:15]([CH2:11][C:10](=[O:12])[C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:9][CH:8]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 5228211-(4-(Trifluoromethoxy)phenyl)ethan-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 86711957HCID 86711957, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-(trifluoromethoxy)phenyl)ethanone (5.0 g, 24.5 mmol) and diethyl oxalate (4.3 g, 29.4 mmol) in MeOH (60 mL) was added NaOMe (30% in MeOH, 5.3 g, 29.4 mmol). The mixture was stirred at RT for 4 h and then concentrated under reduced pressure. The residue was treated with 2N aq. HCl (15 mL) and extracted with EtOAc (2×100 mL). The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford methyl 2,4-dioxo-4-(4-(trifluoromethoxy)phenyl)butanoate as a brown oil (6.85 g, 96%), which was used in the next step without further purification. MS (ES+) C12H9F3O5 requires: 290. found: 291 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was treated with 2N aq. HCl (15 mL)
  3. extractionextracted with EtOAc (2×100 mL)
  4. washThe organic layer was washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-713a1118ac7f40578e25a15d10aa120e
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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